31249-95-3

Usage

Chemical Properties

transparent to off-white flakes

InChI:InChI=1/C10H22N2O3/c1-5-13-6-2-12-4-8-15-10-9-14-7-3-11-1/h11-12H,1-10H2/p+2

Upstream product

• 50977-92-9 1,14-dihydroxy-3,12-diaza-6,9-dioxatetradecane 
• 2752-17-2 2,2'-diaminodiethyl ether 
• 36839-55-1 1,2-bis-(2-iodoethoxy)ethane 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 19249-03-7 triethylene glycol di-(p-toluenesulfonate) 
• 59559-06-7 1,8-diazido-3,6-dioxaoctane 
• 54665-51-9 3,6-dioxaoctanedioic acid dimethylester 
• 929-59-9 3,6-dioxa-1,8-diaminooctane 
• 59945-35-6 N,N'-((ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl))bis(4-methylbenzenesulfonamide) 
• 31255-10-4 1,2-bis-(2-bromo-ethoxy)-ethane 
• 94195-16-1 7,13-dibenzyl-7,13-diaza-1,4,10-trioxacyclopentadecane 
• 136809-46-6 1,10-diaza-4,7,13-trioxacyclopentadeca-2,9-dione 
• 74461-33-9 7,13-bis(p-tolylsulphonyl)-1,4,10-trioxa-7,13-diazacyclopentadecane 
• 30989-20-9 1,4,10-trioxa-7,13-diaza-cyclopentadecane-8,12-dione 

Downstream Products

• 130985-64-7 N,N'-bis(2-pyridylmethyl)diaza-15-crown-5 
• 137918-80-0 7,13-Bis(1'-nitro-3'-(trifluoromethyl)-6'-phenyl)-1,4,10-trioxa-7,13-diazacyclopentadecane 
• 226936-26-1 7,13-bis<4-(1-oxopropyl)phenyl>-1,4,10-trioxa-7,13-diazacyclopentadecane 
• 864511-99-9 C₂₈H₃₄N₂O₉ 
• 145657-12-1 14-(4-Nitro-phenylazo)-4,7,20-trioxa-1,10-diaza-tricyclo[8.7.5.1^12,16]tricosa-12,14,16⁽²³⁾-trien-23-ol 
• 1352942-46-1 C₃₂H₅₀N₆O₃ 
• 1352942-48-3 C₄₂H₇₂N₈O₆ 

Relevant academic research and scientific papers

An Improved One-Step Method to Prepare Diaza-crown Ethers and the Cation Complexation Properties of 4,10-Diaza-18-Crown-6 with Two Transition Metal Ions

4,10-Diaza-15-crown-5, 4,10-diaza-18-crown-6, 4,13-diaza-21-crown-7, and 4,16-diaza-24-crown-8 were prepared by an improved method from the appropriate oligothylene glycol diiodides and diamines.The thermodynamic values of log K, ΔH and ΔS for the interaction of 4,10-diaza-18-crown-6 with Pb2+ and Ag+ were determined by a calorimetric titration method and compared with thermodynamic values for interactions of 4,13-diaza-18-crown-6 with the same cations.The thermodynamic values were found to be different for the two diaza-crown ligands. 4,10-Diaza-18-crown-6 and its 4,13-diaza-crown analog formed precipitates when treated with Co2+, Cd2+, Cu2+, and Ni2+ so that no thermodynamic data are reported for these interactions.

KINETIC AND EQUILIBRIUM STUDIES OF THE REACTION OF 1,3,5-TRINITROBENZENE WITH CRYPTANDS IN ACETONITRILE

Kinetic and equilibrium data for the formation of the adduct from 1,3,5-trinitrobenzene (TNB) with cryptands (221, 222, 21, 22 and di-(Ph-CH2)22) in acetonitrile are reported.The influence of structure and pKa of cryptands on the rate constants, activation and reaction parameters are discussed.A reaction mechanism between TNB and different cryptands has been proposed.

The Complexation of Alkaline Cations by Crown Ethers and Cryptand in Acetone

Stability constants and thermodynamic values for the complex formation of alkali ions by crown ethers, diaza crown ethers and cryptands have been measured by means of potentiometric and calorimetric titrations in acetone as solvent.The interactions between the ligands and solvent molecules play an important role for the complex formation.Cryptands form the most stable complexes with alkali ions if inclusion complexes are formed.Even in the case that the salts are not completely dissociated in acetone the presence of ion pairs does not influence the calculated values of the stability constants.

A General Method for the Synthesis of Diazacoronands

α,ω-Diamino aliphatic ethers react under ambient conditions with dimethyl α,ω-dicarboxylates, in methanol as a solvent, to give the cyclic diamides in good yields, and their subsequent reduction with lithium aluminium hydride affords the respective diazacoronands.

MACROHETEROCYCES. XXXVI. A CONVENIENT METHOD FOR SYNTHESIS OF DI- AND POLYAZACROWN ETHERS

A method is proposed for the production of di- and polyazacrown ethers by the condensation of bissulfonamides with dibromides or ditosyloxy derivatives in a two-phase aqueous alkali-toluene (benzene) system.The optimum concentration range for the substrate and the alkylating agent is 0.017-0.1 M.The catalytic activity of the quaternary ammonium salts decreases in the order (Bu)4NI > (Bu4)NBr > (Bu4)NCl > (Bu4)NHSO4 > (C2H5)3C6H5CH2NCl >> (Et)4NI > (Et)4NBr.The highest yields of te 12-membered azacrown ethers are obtained in the presence of lithium hyroxide, and the largest yields of the crown ethers with larger ring sizes are obtained in the presence of sodium or potassium hydroxide, and this is probably due to the matrix effects of the cation.

MACROHETEROCYCLES. PART 44. FACILE SYNTHESIS OF AZACROWN ETHERS AND CRYPTANDS IN A TWO-PHASE SYSTEM

A facile procedure is proposed for the preparation of azacrown ethers and cryptands by condensation of dibromides or ethylene glycol bis(toluene-p-sulphonate)s with acyclic bis(sulphonamide)s or with bisdiazacrown ethers, respectively.The reaction was carried out in a two-phase system of aqueous alkali-toluene (benzene)in the presence of quaternary ammonium salts as phase transfer catalysts.The catalytic activity decreased in the sequence: Bu4NI ca.Bu4NBr > Bu4NCl > Bu4NHSO4 > Et3NCH2C6H5NCl.Maximum yields of twelve-membered azacrown ethers are obtained when lithium hydroxide is used, while crown ethers of larger size are observed in the presence of sodium or potassium hydroxides; this may be due to a template effect.

Syntheses and Binding Properties of Bibracchial Lariat Ethers (BIBLEs): Survey of Synthetic Methods and Cation Selectivities

A new, two-step method for the synthesis of 4,10-diaza-15-crown-5 and 4,13-diaza-18-crown-6 and their N,N'-disubstituted derivatives from bis(secondary amines) and 1,2-bis(2-iodoethoxy)ethane is described.Essentially, the method utilizes the incipient sidearms as nitrogen-protecting groups prior to cyclization.The yields for cyclization are high, ranging from 32percent to 77percent.The N,N'-disubstituted derivatives of 4,10-diaza-15-crown-5 produced by alkylation or acylation (A), acylation followed by reduction (AR), cyclization (C), hydrogenolysis (H), or single-step cyclization (O) have the following sidearms: H (H, 91percent), MeOCH2CH2 (C, 38percent), EtOCOCH2 (A, 62percent), PhCH2 (C,72percent), 2-MeOPh (C, 52percent), 2-furanylmethyl (C, 67percent), and 2-nitrobenzyl (A, 50percent).N,N'-Dibenzyl-4,10-diaza-18-crown-6 was obtained by cyclization in 63percent yield.The N,N'-disubstituted derivatives of 4,13-diaza-18-crown-6 produced with the new method have the following sidearms: H (H, 92percent), CO-Et (A, 100percent), n-propyl (AR, 78percent), n-butyl (C, 77percent), n-hexyl (C, 32percent; A, 50percent; O, 7percent), n-octyl (AR, 45percent), CO-n-heptyl (A, 71percent), n-nonyl (O, 11percent;A, 45percent;AR, 39percent), CO-n-undecyl (A, 87percent), n-tetradecyl (AR, 26percent), CO-n-tridecyl (A, 78percent), n-hexadecyl (A, 25percent), n-octadecyl (AR, 60percent), CO-n-heptadecyl (A, 100percent), allyl (O, 26percent), propargyl (O, 22percent), HOCH2CH2 (O, 28percent), MeOCH2CH2 (C, 43percent; AR, 76percent), HOCOCH2 (hydrolysis, 81percent), EtOCOCH2 (A, 92percent), PhCH2 (O, 29percent;C, 66percent), 2-furanylmethyl (O, 27percent, C, 62percent), 2-hydroxybenzyl (A, 85percent), 2-methoxybenzyl (O, 30percent), 2-cyanobenzyl (A, 95percent), 2-nitrobenzyl (A, 90percent), 3-nitrobenzyl (A, 95percent), and 4-nitrobenzyl (A, 70percent).The new cyclization method is compared with other, previously published cyclization reactions with respect to overall yield and ease of purification.When this new cyclization cannot be used, diaza crown ethers can be prepared by alkylation of 4,10-diaza-15-crown-5 or 4,13-diaza-18-crown-6.The homogeneous equilibrium cation binding constants (log Ks) have been determined in anhydrous methanol solution for many of the compounds described herein with Na+, K+, and Ca+.The cation selectivities are rationalized in terms of polar, structural, and lipophilicity effects.

NOVEL SYNTHETIC ACCESS TO 15- AND 18-MEMBERED RING. DIAZA-BIBRACCHIAL LARIAT ETHERS (BiBLEs) AND A STUDY OF SIDEARM-MACRORING. COOPERATIVITY IN CATION BINDING

An extremely practical synthesis of 4,10-diaza-15-crown-5, 4,13-diaza-18-crown-6, and symmetrically N,N'-disubstituted derivatives thereof, is presented along with the first survey of cation binding data for the 15-membered ring systems.

SYNTHESIS OF N-UNSUBSTITUTED DI- AND TRIAZA CROWN ETHERS.

Facile syntheses of di- and triaza crown ethers by intramolecular cyclization of oligoethylene glycols containing two or three imino groups or by their intermolecular cyclization with oligoethylene glycol bis(p-toluenesulfonate)s are described.